40 Days of Dating
by usedtoromanticize
Summary: Kurt Hummel is a hopeless romantic who jumps into relationships too quickly. Sebastian Smythe doesn't do commitment and tends to date many people at the same time. People have said that it takes forty days to change a bad habit. But is it really enough? For forty days, two boys with opposite problems will date. Along the way, they may fall in love or fall apart.
1. Preface

**This story is based off of the blog fortydaysofdating.**

**So basically these two people are friends. One of them is a hopeless romantic and the other doesn't really like commitment. The blog follows them as they date for forty days to see where it goes. Plus, they're both designers and they make something for each day and it looks really cool. It's pretty great. You should definitely check it out! It's at **

**I thought the idea of the blog fit really well with Kurt and Sebastian and I couldn't get the thought out of my head so I started this story :)**

**Disclaimer: I do not own Glee (as much as I wish I do..) or the fortydaysofdating blog.**

* * *

"So we're doing this?"

The green eyed boy gave his signature smirk. "I guess we are."

_What have I got myself into?_

The same thought had plagued Kurt's mind for the better part of the week. Ever since happening upon Sebastian in New York a few months ago, they had sort of been friends. The whole cliché 'clean slate', and 'let's put everything behind us' thing was in effect. After all, taking the whole Blaine being Kurt's boyfriend thing out of the situation left them with no real grudges the other as a person. In fact, they found that they were quite similar in their snarky exteriors and ability to give as good as they got

They had become friends. Nothing more, nothing less. Until a week ago.

Of course, Kurt knew that he was a hopeless romantic. He fell for others way too quickly, which did not always give a positive outcome. His heart had been broken many times, and it seemed like he continued to make the same mistakes. But he couldn't help it. Really. Though he didn't particularly mind being single, it was nice to have a constant in his life. Someone that he could love, laugh with, support, and receive the same in return. And cuddles. Cuddles are pretty great.

But how many failed relationships is too many? His last one had been about a year and a half ago. They had loved each other a lot, had lived together, and even had a dog. Then Kurt found out that his (former) boyfriend had been lying to him for quite a while. And it all fell apart from there.

And now? Well, he found he was about to date one Sebastian Smythe for forty days. After all, what did he have to lose?

.::.

Forty days. With Kurt Hummel.

His high school self would have been appalled.

But ever since high school ended and he went to New York, Sebastian Smythe had changed and matured. Like he was a new man. It sounded cliché, but it was the truth. He still dated around, that was without a doubt. But now it was more actual dating and less hook-ups-in-the-bathroom-of-a-seedy-club. That was quite some progress if he said so himself.

Commitment had never been his thing. Why stick to one person, especially when he was in a city full of so many interesting and gorgeous people? Where was the thrill in that? It's not like he was against relationships. He just didn't see the point of rushing into them. Sebastian figured he hadn't found the right guy yet, so why not have some fun along the way?

And there had been times when he had thought he was close. Like two years ago, he had someone. It just hadn't worked out and that was it. There hadn't been anyone he'd been dating steadily since then, just flings here and there. And that's just how he liked it.

But after a while, it did grow tiring.

With every new face, there came a new problem. Too boring, never shuts up, too annoying, too loud, too clingy… He'd been through it all. And more. It would be nice to find someone just right, or even just tolerable instead of several mediocre dates with people he couldn't stand for more than an hour or two, sometimes less.

Sebastian still wasn't quite looking to settle down just yet; that's hard to do in a city like New York, where everyone is so busy trying to make it big or make it at all. But it would be nice to have someone in it with him, a constant in a city where life flies by so fast.

And that's where Kurt came in.

.::.

Both boys weren't sure if anything good would come out of this. Before, they couldn't stand being in the same room for more than ten minutes. What made them think they could stand constantly being together for forty days? Though they had matured, they were still the same people. There was no guarantee that this would work out. Hell, there was no guarantee they would still be friends after this.

But really, where was the fun if there wasn't a little risk?


	2. Day 1

**So here's Day 1!**

**Disclaimer: I (sadly) do not own Glee or fortydaysofdating**

* * *

_From: Sebastian Smythe_

_Happy first day of Spring!_

_I had no clue when we set the date._

_Coincidence?_

_So…Fat Radish to celebrate after class tonight?_

Sebastian would not admit it, but it took him way longer than necessary to type out a message. He had to make it perfect. Everything had to be perfect. It was their first date. He didn't want to screw this up. But he couldn't seem overeager. Because he wasn't. Of course not. He's _Sebastian Smythe._

.::.

Kurt grinned at his reflection, nodding his approval for himself. He looked pretty good if he said so himself. His hair was coiffed to perfection and his outfit looked amazing. White button up, charcoal vest, dark jeans, and a baby blue bow tie that made his azure eyes stand out.

He glanced at the clock, grinning when Sebastian's card caught his eye. After class, Sebastian had had a friend deliver a lollipop with a cute little note.

_Me + You x 40. Ready?_

Kurt was so ready.

.::.

"Damn. I look good." Sebastian murmured as he appraised himself in the mirror. He may sound cocky, but it was true. He looked _hot. _Well, he always did, of course. But there was a sort of pride in getting ready and looking great for a big date. And this was a big date.

He finished buttoning up his forest green shirt, adding a sleek black tie. Green. A very spring-ish color, considering it was the first day of spring. He hadn't even noticed until this morning. But it felt like an omen. Like this thing with Kurt was a new beginning, and it could possibly blossom into something more. That is, if they could stand each other more than they used to.

The first date, though. It was a big thing. A sort of swan song to singlehood for both of them.

.::.

So Kurt was a bit early, but hey, he was excited. And nervous. Mostly nervous. It was only fifteen minutes, but it was a chilly night. He shivered, wishing he had brought a coat. The vest didn't exactly keep him warm, considering it didn't have sleeves. And vests weren't meant for warmth. Damn weatherman had said it would be warmer.

He and Sebastian had planned to meet outside of the restaurant, which was where he was currently standing and shivering. He spun around, sagging with relief at the sound of the familiar voice.

"Hey, Princess," Sebastian greeted with a wink. That nickname was a habit he never seemed to break, but Kurt was fine with it now that they were friends and he knew there was no real spite behind the words. Sebastian gave Kurt a once over, just as Kurt was doing.

Kurt gave him a sincere grin. "Hi, Meerkat."

"We should probably get inside. You look like you might be turning blue."

Sebastian held the door open (Kurt grudgingly admitted to swooning slightly at the chivalry. Just slightly, nothing more!) and led them inside. He told the reservations to the hostess, who led them to their table. They were seated, ordered drinks, and discussed the menu for awhile.

"Oh, I almost forgot! I have something for you!" Kurt exclaimed as soon as they had ordered their food. He pulled out a box and slid it across the table.

Sebastian eyed the box for a second before lifting the lid off. He pulled out the first item and arched an eyebrow at Kurt questioningly. "Beer?"

Kurt laughed, "It's a sort of 'care package' to help you get through the next forty days."

"Of course, I'll definitely need these, especially the beer," Sebastian chuckled good-naturedly. He continued pulling out the contents. A box of pills for headaches. Pills for tiredness. A pen. His eyes lit up and he smiled widely as he pulled out the last of the objects in the box. "You remembered!"

"Oh yeah, the Clif bars?" Kurt grinned back at him, "I remember you would always be eating them when we hang out. So I figured you must like them, right?"

"Yeah, I love them. Thanks, Kurt, this is great!"

.::.

It had been a great night. They had spent a lot of time talking, getting to know each other on a deeper level, and bickering over nothing, because they just wouldn't be Kurt and Sebastian without some playful banter.

They talked. A lot. Kurt told Sebastian about his family. How his parents met and married when they were young, and it worked out for awhile. How he lost his mom when he was eight. How much he loves his dad and misses his mom, even though he also loves the new little family that was formed when Burt and Carole got married. He told of how proud he is of his dad becoming a Congressman, especially when he had started as a mechanic in his self-made business.

They conversed about Sebastian's dating habits. There always seemed to be a guy he liked, one he had been seeing and was losing interest in, and one he was planning on breaking up with. It was like a constant cycle, and he was getting tired of it. He was happy that they were doing this Forty Days of Dating project. They both agreed that it was a refreshing change from their usual lives.

So far, so good. The first date was a success.

"So should we split the che—?"

"I'm paying," Sebastian interrupted, taking the folder and sliding his sleek black credit card into the card holder.

"Wait, no it's okay I can—"

"I'm paying." He repeated.

"You don't have to," Kurt tried again.

Sebastian shook his head and insisted, "I asked you out on this date. So I'm paying." He snapped the folder shut and handed it to their waitress.

"Fine, but I'm paying next time," Kurt said.

"Whatever floats your boat, Princess."

.::.

It was 1:28 that night (or morning if you looked at it that way) when Sebastian received a text from his one of his friends. They had been talking about this Forty Days of Dating Project for awhile. He seemed pretty excited for Sebastian.

_From: Jeff Sterling_

_March 20 1:28AM_

_Omg I stalked you and this guy Kurt as I'm already so interested in this love drama. He is hawt! You best go for this, son ;-)_

* * *

**For the sake of the story let's pretend Sebastian's friends don't know Kurt very well**

**Hope you liked this! :)**


	3. Day 2

**If you haven't already you should check out the fortydaysofdating blog because this story will make a lot more sense!**

**Also there were rules that the couple have that I forgot to include in the other chapters so I'll just put them here:**

**We will see each other every day for forty days.**

**We will go on at least three dates a week.**

**We will see a couples therapist once a week.**

**We will go on one weekend trip together.**

**We will fill out the daily questionnaire and document everything.**

**We will not see, date, hookup, or have sex with anyone else**

**So I'm using it as a basis for this story. But they wouldn't be doing #5 in the story because there's no blog in the story...**

**Also, to KlaineGleekStarkidfan4eva - I don't know if I'll be including Niff or other couples mainly because I actually have no idea where this story is going to go. I don't know if I'll follow the blog exactly as they go or if I'll change anything. But if it fits in the story I'll try to add them in because Niff is pretty adorable :)**

**Hope you all are liking the story! :)**

**Disclaimer: I don't own glee or fortydaysofdating :(**

* * *

Day 2

"Do we really have to do this?"

"Yes."

"Why?"

Kurt sighed dramatically and gave an exaggerated eye roll as he spun around to face Sebastian, repeating for what felt like the hundredth time, "Because we made rules and this was one of them. Now hurry up or we'll be late!"

With that, he turned on his heel and strutted away, not bothering to check if the other boy was still following him.

"Drama queen," Sebastian muttered, but continued to walk forward.

"I heard that," Kurt informed him.

"You were meant to," he retorted.

So this morning hadn't been the best. It was their first day going to a couple's therapy session, which was one of the rules that they had agreed on for their project. It had seemed rational as they talked about it, but they were both having some second thoughts now that they were actually going. Kurt had gone to therapy sessions on his own before and enjoyed it, but neither of them had gone to a couple's session, so they didn't quite know what to expect.

Finally, they reached the destination with a few minutes to spare. They sat in a room and met their therapist, Jocelyn. She was a pretty brunette who looked to be in her thirties. She smiled warmly and urged Kurt and Sebastian to sit in the dark leather couches as she went to sit behind her desk and pulled out a filing folder.

The woman flipped through a few pages before looking up to face them again, "Kurt Hummel and Sebastian Smythe. I see you two are experimenting with a project where you are dating for forty days?" The two boys glanced at each other and nodded. "Tell me about that."

"Well we've kind of had opposite problems in dating," Kurt began, "And we found ourselves single at the same time…"

"We've been friends for awhile. So we decided to try it out." Sebastian added.

Jocelyn nodded as they spoke, jotting down notes. When they finished speaking, she looked up at them, leaning forward and squinting a bit. "Now tell me, are you two attracted to each other?"

"Uh… I think… Attraction is a funny thing…"

"Well, you see… I just… It's complicated..?"

They looked at and away from each other awkwardly, fumbling for words. That wasn't really something that had been brought up, considering their history.

"Physical attraction is important in a relationship. It's a simple question. Kurt, do you find Sebastian physically attractive?"

Kurt peeked at Sebastian through his peripheral vision, his face flushing red. "Umm…" He squirmed in his seat a little, feeling Sebastian's gaze on the side of his face. It made him blush even more. Why was she singling him out like this? That wasn't fair! "Well…yeah, I guess… yes? He's attractive, yes… Pretty eyes. He's...attractive. Uh. Yeah…"

He could practically _feel_ Sebastian grinning smugly without looking at him. Thankfully, the therapist seemed to accept his stammered answer and turned on Sebastian instead. "And Sebastian, do you find Kurt attractive?

The boy didn't seem to expect her to question him as well. "Um. Yeah, I think… He's pretty… I like his…uh…I like his…face. Yeah." Kurt resisted the urge to snort. In his mind, he flashed back to the Lima Bean and traded insults. But there was no denying Sebastian was insanely hot (no matter how much inner strength it took him to admit it).

Sebastian really did find Kurt really attractive. He'd grown up a lot since high school. Then, he'd had a sort of pretty elegance to him. Now, he was all lean body, luminous skin, high cheekbones, and bright eyes. Definitely attractive. Not that he would really admit it, either.

"Why are you doing this project? Do you have a goal in mind?"

Both boys were snapped from their thoughts. They'd almost forgotten that there was actually someone else in the room. And that they were supposed to be talking to her.

"I think we both wanted to try something new," Sebastian explained. "It was kind of tiring, going through the same things all the time. It's exciting to be trying something new."

Kurt nodded in agreement. "We don't really know what's going to happen. We were just planning on going with it and seeing where it takes us.

Jocelyn nodded, taking more notes. "And if it doesn't work out? Are you ready to be hurt? What would happen if it screwed up your friendship?"

Kurt looked over at Sebastian, biting his lip. This was something they had not discussed. At all. Sebastian looked like he was panicking on the inside. It's not like they'd been friends for a really long time. Even so, Kurt didn't want to ruin it if there was a potential to become something. But relationships are a gamble. He knew that going in. They both did.

He decided to voice his opinion. "Both of us know that it's a possibility that it won't work out. But we're willing to take the risk. If you just play it safe and never take risks, you'll never get anywhere. But I think even if the worst happens, we could still be friends."

Sebastian was staring at him with an unreadable expression and he didn't know what to think of it. Thankfully (or not), Jocelyn continued with her questioning. "How long have you known each other?"

"About four years," Sebastian answered.

"We weren't really friends at the time, though," Kurt added, careful not to give too many details. He didn't want to talk about that quite yet. "We knew each other when we both lived in Ohio, but only reconnected here in New York."

"How long ago was that?"

"A few months, like half a year."

Jocelyn nodded thoughtfully. "So you've known each other for four years, and have been friends for about six months. Why did you never try dating before?"

"A lot of reasons. I never thought we would be compatible," Kurt said. It felt like a more eloquent way of saying he thought Sebastian was an arrogant, overconfident jerk. "We've both changed a lot since we started talking around last September, and a whole lot more since we knew each other in high school. I feel like we're more suited to each other now. I definitely like him a lot better now than I used to."

Sebastian chuckled, remembering their days in high school. "For me, it's more like I wasn't ready to settle down. And I'm still not. I like the freedom of being single. I do like trying this, though. But Kurt knows I have some issues with commitment. I don't want to hurt him and I don't want to risk our friendship, especially since we just got around to being friends. And the thing with us not being compatible." He turned to look at Kurt. "You love love, and that's totally fine. A lot of people do. It's just not what I'm used to. But you jump into things really quickly."

"I know. I just like to try to test it out and get a feel to see if it could become something more," Kurt admitted, "But I think I get invested in people really quickly. And things just happen quickly. Emotions know no boundaries."

For the rest of the session, they discussed a lot of topics that the pair probably never would have breached on their own. It did help them realize the reality of this project. Forty days was a long time. A lot could happen.

Sebastian was starting to feel anxious about this. He hadn't had many relationships that had lasted longer than a few weeks, and even then, he hadn't seen the person every day. With this project, he was seeing Kurt a lot more than probably any other relationship he'd had before. He hadn't realized that this worried him until Kurt had sent him a list of what seemed to be random activities later that day.

"What's this?" Sebastian asked over the phone as he examined the email.

"Date ideas," Kurt answered. "For next week."

"For…what?"

"You know, for the project we've been doing?" Kurt reminded him patiently, "Forty days of dating?"

Sebastian just kept staring at the screen. Date ideas for next week. He was going on more dates with Kurt. A lot more. For forty days. It sounded really overwhelming in his head. "Um, yeah. I just didn't know that you had already started planning."

"Oh, they're just ideas! We don't have to do all, or any of them. I just like having a set schedule, but we could just do things more…spontaneously if you like that better?"

He sounded worried that Sebastian didn't like his ideas, so he hurried to correct himself. "No, these are great! I was just kind of surprised."

"Okay… well I have to go. Tell me if you have any other ideas or anything?"

"Yeah, of course. See you tomorrow."

"See you!"

Sebastian threw his phone on his bed after hanging up. He plopped down, burying his face in his pillow. What had he gotten himself into? He did like Kurt. He was nice and attractive and he liked bantering and talking and hanging out with him. But forty days. What if it didn't work out halfway through? Would they still continue for the rest of the project? He started panicking in his mind about everything that could possibly go wrong.

Sebastian picked up his phone again and scrolled through his contacts. He had really only told a few of his friends about this project, and he needed someone to talk to. Finally, he settled.

_From: Sebastian Smythe_

_March 21, 12:26PM_

_I'm kinda freaking out. I have 39 days left! It's not Kurt, it's just the fact that I have to see someone EVERYDAY_

_From: Hunter Clarington_

_March 21, 12:31PM_

_Just have fun with it. And get used to it unless you want to die alone and sad and bald_

Sebastian rolled his eyes at the text, typing out a snarky reply. His friends sure gave the best advice ever.


	4. Day 3

**Disclaimer: I unfortunately do not own Glee or fortydaysofdating.**

* * *

Day 3

"I found something for us to do for date night," Kurt was saying. They were in a coffee shop, just like old times. But with less insults. They both had work soon, but it was nice to see each other, even just briefly.

"Oh really?" Sebastian asked as he grabbed Kurt's grande nonfat mocha and his own tall caramel macchiato and handed Kurt his drink. "Do tell."

Kurt shook his head with an impish grin. "Not a chance. But I do need to know if you're free tonight, or if tomorrow would be better?"

"Hmm." Sebastian hummed as he sipped his coffee. He hadn't had a free night in around ten days due to his work and just personal stuff. He really wanted to kick back and watch the Knicks game. But they already had a date planned for Sunday night. So he figured it would be better if they went today rather than Saturday. "Tonight."

"Okay! I've got to get going, but I'll talk to you later! Bye!"

Sebastian stared after Kurt as he practically ran out the door. He wondered what there was in store for tonight.

.::.

Kurt called during his lunch break. "Hi!"

"Hey."

"Well you don't sound very excited," Kurt teased. "And to think, I was just about to reveal my fabulous plans for tonight!"

Sebastian scoffed, "Well you certainly didn't reveal much with your hasty getaway this morning."

"Oh, right… Sorry about that." Kurt suddenly felt guilty. He hadn't meant to seem rude; he just realized he'd been short on time. "I forgot that I had to give some designs to Isabelle, and I hadn't noticed how fast time went by. I'm sorry…"

"Kurt, it's fine. I was kidding. I'm not mad or anything," Sebastian assured him.

"Okay, good. Because tonight we are going to see the off-Broadway play _Really, Really_!"

"Oh, I think I've heard about that."

"Great! Well, it's at 8 o'clock at the Lucille Lortel Theatre. Do you know where that is or do you need directions or anything?"

"I'm sure I can figure it out. So I'll see you there?"

"Yeah, see you!" Kurt grinned. He felt like it would be a good night.

.::.

It wasn't until later that evening that Sebastian realized that they hadn't even arranged when/where they were going to meet up. They hadn't even communicated since the phone call. So he took it upon himself to set it up.

_From: Sebastian Smythe_

_March 22, 6:19PM_

_Hey hey. Meet me in front of the theater at 7:45?_

He busied himself with picking out an outfit as he waited for Kurt's response. A t-shirt seemed too casual, but he didn't want to be overdressed, either. He settled on an outfit similar to what he wore at the restaurant: a simple button up shirt, but dark red this time, with black jeans. By the time he was dressed, Kurt hadn't replied, so he shot him another text.

_From: Sebastian Smythe_

_March 22, 6:42PM_

_or we could grab a drink before hand if you want…_

He spent some time coiffing his hair until he was satisfied. A once-over in the mirror and he was ready to go. Checking his phone, he noticed that quite some time had passed since his last message, and Kurt still hadn't replied. Sebastian decided to head out, anyways. According to Google Maps, there was a little bookstore near the theatre. He could just wait for Kurt there.

Half an hour passed. It had been an hour since his first message, and there was still no word from Kurt at all. Sebastian was starting to get a little frustrated. And worried.

_From: Sebastian Smythe_

_March 22, 7:26PM_

_So I'm at the bookstore down the street now. Where are you?_

When there was no response, he decided to call. It rang and rang and rang, then went to voicemail. Sebastian groaned, but started speaking when he heard the beep.

"Um, hey, Kurt. I don't know if you saw my messages but I'm here by the theatre…well, a bookstore near it. Uh…Where are you? I haven't heard from you since you called during lunch and I'm getting kind of worried… Call me back? Bye."

_From: Sebastian Smythe_

_March 22, 7:39PM_

_Just called and left a message. Are you standing me up?_

Sebastian sighed, running a hand through his hair. Well this sucked. It had been around seven hours since he'd talked to Kurt at all. If this was him cancelling…well, he could have at least given him a heads up. He was walking out of the bookstore when his phone started vibrating in his pocket, signaling a call. He pulled it out. It was Kurt. He didn't know whether he should be relieved or pissed.

"Kurt?"

"Sebastian! Oh my gosh, I'm so sorry!" Kurt exclaimed hysterically, "I was getting ready and I didn't check my phone so I didn't see your message until like now! I'm so sorry, I'm on my way over right now!"

"Hey, it's okay," Sebastian told him. Sure he'd been upset before, but at least now he knew that Kurt was okay. And he'd never heard him sound this frantic before; it was kind of adorable. "I'm in front of the theatre now. Meet me here?"

"Yes! I'll be there in like five minutes."

"Okay," Sebastian said.

"Okay," Kurt echoed.

True to his word, Kurt arrived in front of the theatre in about five minutes. His face was flushed and his breathing was a little heavy from his rush to get there. "Hi."

Sebastian smiled widely at the sight of him. "Hey."

"I'm really sorry about that. I should probably check my phone more. I had a really crazy day at work today and I just forget sometimes. Sorry."

"No, it's okay. I probably should've known that you don't check your phone much. We probably should've arranged meeting times before. So I guess we're both at fault?"

"I guess…" Kurt gave a half-hearted smile. He still felt extremely guilty, but it was nice that Sebastian wasn't one to stay annoyed or hold grudges.

"Shall we be going in?" Sebastian asked in a posh voice, offering his arm with a flourish.

Kurt giggled and took his arm. "We shall."

The play was great. To Kurt. He found the dynamics of all the characters intriguing. Sebastian thought it was alright. It was difficult to empathize with any of the characters. And he felt like Kurt caught him checking the Knicks scores on his phone halfway through.

After the play, they went out for drinks. Sebastian told Kurt about his last real relationship. He'd really liked the guy, but he'd taken a job in San Francisco. Sebastian didn't think long distance would work out, so he broke it off. He felt bad about it, but thought that the choice was better for the both of them.

"I think you made the right decision," Kurt had commented. "Now, I know it's different for everyone, but long distance is hard. I've been there and look where that got me. And that was only between Ohio and New York for a few weeks." He smiled bitterly. "There's almost three thousand miles between California and New York. Some relationships can withstand a lot, but being that far for an extended period of time… that seems like more than most couples could handle."

They opened up to each other a lot. They even talked about what had happened back in senior year, but mostly left that topic alone. It was a sensitive subject. Kurt found the courage to tell Sebastian about high school. About why he transferred to Dalton.

"I'm glad that you trust me enough to open up about that. I don't know what it's like at a public school since my parents have sent me to private schools all my life, but it sounds terrible. And I'm sorry you had to go through that. But hey, look how much stronger it made you." Sebastian had said with the sincerest look in his eyes. He was a good listener and easy to talk to. Kurt liked that about him. He'd found that there weren't many people that he could talk to about the past.

He didn't like to spend too much time looking back on what was already said and done. It's not like he could change what happened. But it was nice to have someone to talk to about it.

At the end of the night, Sebastian insisted on walking Kurt home. Kurt was exploding with joy. He really was a sucker for the gentlemanliness. And lately, Sebastian had been the epitome of a perfect, chivalrous gentleman. They had both really enjoyed their time together, and they were a lot closer after sharing their stories.

They stopped at the entrance of Kurt's apartment complex.

"So…I'll see you tomorrow?" Kurt asked tentatively, smiling shyly.

"Yeah…tomorrow," Sebastian answered, his mouth forming a crooked grin.

"Okay."

"Okay."


	5. Day 4

**So I don't actually know that much about locations in New York besides what I've found off of google... I hope I'm not too far off..**

**Please love me or I will wilt like a flower :(**

**Hope you all like it! 3**

**Disclaimer: I don't own glee or fortydaysofdating**

* * *

Day 4

Kurt had _just_ thrown his bag on his desk and started on his work when his phone started ringing. He groaned at the thought of having to go all the way across the room to retrieve it from where it was charging. It had been a long day of gallery hopping in Chelsea, and he still had a lot of work to finish. Somehow, he forced himself to get up and pick up his phone. He automatically brightened with a grin when he saw that is was Sebastian. They hadn't talked all day and he was suddenly feeling elated.

"Sebastian! Hi!" Kurt coughed awkwardly, realizing how high and squealy he probably sounded before schooling his voice into a lower pitch. "Uh, I mean. Hey."

He could hear the other boy snickering over the line, but decided to let it slide _just this once. _He tucked the phone between his ear and shoulder as he continued to do his work.

"So I'm heading home from work soon and I need to pick up some groceries. Fancy joining me? You can bask in my glory while getting food. Pretty great deal if I say so myself," Sebastian joked.

"Wow, who could resist that? Food _and_ I get to spend time with such a humble and modest being!"

"Don't use that tone with me, Princess!"

"I don't know what you're talking about, meerkat," Kurt said in the most innocent voice he could manage. Which sounded pretty innocent. He was a pretty amazing actor, after all.

"Anyways," Sebastian interrupted his thoughts of self-praise, "One of the rules of this project was that we have to see each other every day, which we have yet to do today."

Kurt sighed over-dramatically into the phone, "Well, I guess I have to then. I mean, I'm practically being forced to see your stupid face."

"You love my stupid face. So meet me at the Union Square Whole Foods later?"

"Whole Foods? What about West Side Market?" Kurt suggested. To be honest, he really just wanted to go to West Side Market because it was right on the bottom floor of his apartment. He would often go there to make important decisions, such as which chocolate to buy that wouldn't give him pear hips.

"But Whole Foods has my organic orange juice."

"Your what?"

"Nothing. But I think we both know Whole Foods is obviously better!"

"No!" Kurt protested, "That's definitely not true. West Side Market has a lot of fresh foods. Plus, it's cheaper than Whole Foods. I need to have money for other things besides food, you know?"

Sebastian whined petulantly, "Whole Foods is still better!"

"Well we obviously can't make a decision by ourselves. So what do we do?"

"Flip a coin?"

"Okay, let's do that."

"Hold on, I think I have a coin."

Kurt could hear what he assumed was Sebastian putting the phone down and rummaging through his wallet for a coin.

"Got it!" Sebastian declared triumphantly. "I'll even let you take your pick first."

"Heads…wait!" Kurt exclaimed, suddenly thinking of something.

"What?"

"We're on the phone! How will I know if you're being fair? You could totally just say it landed on tails so that we would have to go to Whole Foods?"

He could practically hear Sebastian rolling his eyes in the brief silence that followed. "Do you want me to get a witness or something?"

"Yes!"

"You're impossible," Sebastian was mumbling under his breath, but Kurt heard him call out away from the phone, "Hey, Nick! Can you help me with a thing? Just come here! It'll take like two seconds! I don't care if Jeff's waiting for you! Just for a second, c'mon!"

Kurt chuckled to himself as he heard Nick's grumbling as he finally complied.

"Kurt, you still there?"

"I am in deed," Kurt confirmed.

"Okay, Nick, when I flip this coin, say what it lands on, okay?"

There was a moment of silence and then a little _ping_ as the coin landed on a table. Kurt waited with bated breath; this was the ultimate decision of whether he'd have to make an effort to leave the building.

"Heads!" Nick proclaimed.

"Laziness prevails!" Kurt crowed excitedly. He laughed as he heard Sebastian sighing exaggeratedly in the background.

"Fine, I guess I'll come over there then."

.::.

"Hello, Sebastian! Lovely to see you here in this charming little market!" Kurt greeted him a little too brightly.

Sebastian rolled his eyes, "Whatever, they better have my orange juice!"

They walked in and each grabbed a basket. The store was actually quite small, though there were numerous shelves packed full of products crammed into the tiny space. The fruit aisle was first. Sebastian picked up two boxes of blueberries and some bananas while Kurt picked out a box of strawberries.

As they walked around, Sebastian accumulated a small hoard of junk food. This included cheddar puffs, pizza pockets, miniature corn muffins, Napolitaner wafers, and cereal. Lots of cereal.

"Why do you need so much cereal?" Kurt inquired, eyeing the four boxes in Sebastian's basket.

"To eat? What else do you do with cereal? Bathe in it?"

"How do you eat that much, though? What if you ate so much cereal that you just spontaneously combusted and exploded? And then on your tombstone it would say, _Here lies Sebastian Smythe; he ate too much cereal and exploded._"

"I'm from Ohio, what do you want from me? I like my grains!"

"You seem to have forgotten that I'm from Ohio, too, but you don't see me potentially putting myself at risk of exploding from cereal."

Sebastian gave him a half amused, half confused look. They continued on to the refrigerated sections of the store.

"I really hope they have my almond milk," Sebastian said, mostly to himself.

"Almond milk?"

"Yes. It's healthy and delicious."

He grinned in triumph when he found his almond milk and added it to his stack of what was mostly cereal. "Now I need my organic orange juice."

"Is this it?" Kurt asked, pointing through the glass door at a carton of juice.

"No, that's not the right brand. I'm looking for a certain one," Sebastian explained, "I'm not sure if they have it here. A lot of stores don't."

He told Kurt the brand so they could both look for it. A few minutes passed and neither of them had seen the brand of Sebastian's specific organic orange juice.

"Are you sure none of these other juices are okay? They're all organic. And made of oranges."

Sebastian shook his head. "No, I _need_ this brand!"

Kurt giggled, "I never thought you would be so picky about your orange juice."

"Shut up," Sebastian muttered, bumping Kurt's shoulder with his own, "You're picky about literally everything else. So you have no room to talk."

"True," Kurt shrugged. At least he could admit his problem. He decided to check his messages while Sebastian continued his quest for his special orange juice.

"I found it!" Sebastian suddenly shouted triumphantly after a few more minutes, seemingly appearing out of thin air behind Kurt.

"AH!" Kurt squealed, his phone slipping from his grasp and clattering to the ground when Sebastian startled him into accidentally dropping it.

Sebastian sniggered at his reaction, but at least had the decency to pick up his fallen phone for him. Thankfully, the screen didn't crack.

"Is that Blaine Anderson? Why is he sending you random numbers?" Sebastian asked curiously. He'd seen what was open on Kurt's phone at the moment.

"Oh, it's nothing," Kurt chuckled awkwardly, "Well, I went on a date with him the night before we started our project and I told him about it and that we had a rule that we can't date other people. So…he's been sending me a countdown. Everyday…"

Sebastian raised his eyebrows at him. "A countdown?"

"Um, yeah. A countdown for the days left of the project…"

"Oh…"

"…Yeah…"

They were both silent for a beat. After all, was there a book about what to say when you're dating a guy for a forty-day project thing and the guy's ex boyfriend, who cheated on him and they broke up but had a thing and went on a few dates after that, was emailing the guy you're dating a countdown for your forty-day project to be over? Uh, yeah. Sebastian highly doubted it.

Kurt finally broke the silence. "So…should we go check out now?"

It took a second for Sebastian to snap out of his thoughts. "Oh yeah, right. Check out. We should do that. Because we have groceries. And we have to do that. Check out. Right. Good."

They each paid for their groceries and took the bags. Since Kurt's apartment was right above the market, they stood outside to say their goodbyes.

"So…this was fun," Kurt said.

"Yeah, it was," Sebastian smiled genuinely. It had been. Maybe it was a bit awkward with the thing about Blaine, but the rest had been fun. He learned a bit more about Kurt and his little quirks. He'd also realized that he hadn't felt the urge to talk to other guys since he'd started seeing Kurt regularly. As little as the time they'd spent together was, he still loved every moment. It was pretty great.


	6. Day 5

**I'm so sorry for the lack of updates! D:**

**This story actually has gotten a lot more reads than I expected...it's exciting. I hope you're all liking it! :)**

**To be honest, I have no idea where this story is going. Or if it's going anywhere at all. It's fun to write, though.**

**Reviews are much appreciated!**

**Hope you enjoy, lovelies!**

**Disclaimer: I don't own anythinggg**

* * *

Day 5

Sebastian knocked on Kurt's door at nine a.m. sharp with art supplies, coffee, and cookies in tow. The door swung open to reveal a beaming Kurt.

"Hi! Come on in!"

Sebastian walked in to find the space of Kurt's living room totally transformed. Most of his furniture was pushed to the sides of the room to make space for the passive cover in the middle. On top of it were multiple canvases, paper, paint, brushes, and an abundance of other supplies. It was all for the activity they'd planned for the day: art therapy. Or more specifically, art therapy about their relationship histories.

"I brought coffee," Sebastian told him, offering Kurt the cup of his usual. "And some snacks for while we're painting."

"Are these from Birch Coffee?"

"Yeah, I know they're your favorite."

Kurt accepted the coffee graciously and inhaled its warm, sweet aroma. "You're the best."

"I know," Sebastian responded with a wink, sipping his own coffee.

The other boy rolled his eyes, placing his coffee on a table at the side of the room. Sebastian followed suit, placing the package of cookies there, too.

"So, I thought we could start right off. Straight to the point."

"Okay, what's first?"

Kurt picked up two medium-sized canvases, handing one to Sebastian. "We're making numbered lists with every person we've ever been on a date with."

_Oh, God. _Sebastian thought. He'd been on lots of dates. Lots. Most of them were just one time things, but still. _Lots._

"Okay, let's do this."

.::.

Kurt had been finished with his list for about fifteen minutes, casually sitting to the side sipping his coffee and nibbling on ginger cookies. Sebastian was still working on his list, struggling to remember the name of every person. It made Kurt wonder how many dates he'd been on, as Sebastian refused to let him see the canvas until he was done. In the mean time, Kurt had figured out how serious he'd been with each of the people he'd been on dates with.

He'd dated twelve people. He had kissed eleven guys and one girl, that girl being Brittany in sophomore year of high school. He had two serious long-term relationships and three somewhat serious ones. He'd been in love twice, and he had been on more dates this last year than the rest of his life combined.

"Done!" Sebastian declared at last. He turned his canvas around so that Kurt could see it.

The boy's blue eyes widened to the size of saucers. "Sixty-five!"

Sebastian nodded with a smirk. It felt kind of nice to share this with Kurt. No hiding. It was liberating. He shrugged. "It's not like most of them meant much. A lot I dated them once and lost interest."

"So if you counted ones that lasted longer than one date…?"

"It would probably be less than half of the list," Sebastian replied.

Kurt nodded thoughtfully before suddenly tossing the bag of cookies to Sebastian. "You should eat some before I eat them all and explode of too many ginger cookies."

"There's no such thing as too many cookies. But hey, at least you know I'll be there with you, exploding from too much cereal."

Kurt rolled his eyes, walking over to sit down next to Sebastian and admire their canvases. They looked quite pretty, with bold text painted over splashes of bright hues. He turned to smile at the boy beside him. "It's nice isn't it?"

"Ginger cookies and cereal?"

"No," Kurt laughed, "Well, yes. But that's not what I was talking about. This. Art therapy. It's like airing our dirty laundry. Except I never thought I would like sharing it with someone."

.::.

The better part of the afternoon was spent painting about past relationships that had been most significant to them, just a short phrase about that particular person. Prominent, dark words contrasted beautifully with the stark white of the canvases. They had painted ten each, and were giving telling each other about their history with each person.

Kurt was explaining, gesturing to his first canvas. It read, 'We were young & stupid & I forgive you' with a little portrait of a dark-haired man with gelled hair above it. "This one is Blaine."

"Of course."

"I'm guessing you already know all about that?" Sebastian nodded, and Kurt smiled knowingly. "Word travels fast at Dalton, even with ex Warblers. Well, since we're doing this, I'll tell you about it anyways. He was my first love. We dated since my junior year of high school up until a few weeks into college. Then I came to New York and we couldn't handle the long distance. So we broke up. We were just friends for awhile, but we have been together and gone on a few dates since then."

"Oh yes, the emailed countdown," Sebastian remarked.

Kurt snorted. "Yes, that. Tell me about yours, now?"

"With pleasure." Sebastian walked across the room to pick up one of his canvases. On it was inscribed, 'We were walking when we saw a limo parked. I paid the driver $100 to drive us over the Brooklyn Bridge.'

"It was our first date and we just saw a limo. I asked the driver if he could drive us across the bridge and he said he would for $100. So I gave it to him and then we were coasting across the Brooklyn Bridge."

"That sounds amazing."

"It was. Sometimes you have to be spontaneous, you know? So I did that. The view was gorgeous and we both loved it."

"So what happened?"

"I was working a lot around the time we were dating and our relationship kind of fell apart. That was the first time I thought I might be in love, but it just didn't work out."

"I'm sorry," Kurt said sincerely. "I can sort of relate to that. A relationship with potential to become…something, that doesn't work out because of the circumstances."

"Yeah?" Sebastian walked back over as Kurt was pointing out another one of his canvases. 'You were too good to me.'

"His name's Adam. We were college sweethearts. He was great. Cute, sweet, funny, charming, British. But that was around the time after Blaine and I had broken up, and I wasn't completely over it. And we both knew it, but we still tried. I could see that he was putting my happiness before his own, and that's when I could tell it just couldn't work out. He was just too good to me. We broke up on good terms, but I haven't talked to him much since."

Kurt sighed. They hadn't been very serious or anything. But there was always that wishful thinking in the back of his mind. What could have been if circumstances were different? Would things be completely different from how they were? He could only imagine.

"It's the worst," Sebastian agreed, "Not knowing what could have been."

He nodded in the direction of another print. 'I'll always remember you as the one that got away.'

"There was something there. I don't know what, but it was something. We met through a mutual friend and it felt like something just clicked. I didn't really realize that until more recently. But like they say, you never know what you have til it's gone. And I took it all for granted. And before I knew it, he was gone. We were together for a bit more than half a year. I doubt that sounds like a long time, but it's a long time for me. We broke up about two years ago, and I haven't had a long relationship since then. Until now, I guess."

Kurt nodded along empathetically. It was a feeling that he wished didn't exist for anyone anywhere.

He really liked this new side of Sebastian that was so willing to open up. Obviously, people will change in a span of seven or eight years, but it really was amazing to see how the boy had changed. He couldn't help but compare the arrogant, flirtatious boy he had been in high school to this clean-cut, confident, playful man.

He definitely liked seeing Sebastian out of his Dalton uniform and those striped Rugby shirts; the tight t-shirts and button ups suited his toned body much better. His hair was much the same, maybe a shade or two darker from the dark New York winters, yet styled the same if not slightly less obnoxiously CW-esque. His jaw line was sharper, eyes brighter, smile smirkier, if that was possible. The old fire in his words and eyes still burnt bright, but who would Sebastian be without his trademark smirk and snarky retorts? And yes, there was this willingness to open up and talk. It was great. The two had really learned to connect over the past few months, especially the past week.

In his head, Sebastian had also been comparing and contrasting high school Kurt to now-Kurt. He had definitely kept his extravagant wardrobe, though his outfits now seemed slightly toned down, though just as, if not more, high-end and fashionable (Sebastian would never admit that out loud. He wouldn't give Kurt that satisfaction). Kurt appeared undeniably different physically, though. He'd lost that last bit of baby fat, his face more angular and graceful. His hair looked longer and he styled it more elegantly than he had in years past. There was also the fact that he was a lot less closed off and cold than he used to be toward people he wasn't familiar with. Or maybe that was because Sebastian had been hitting on his boyfriend. Yeah, that was probably it.

He thought about how if they hadn't decided to do this project, he probably wouldn't have considered dating Kurt. After all, they were pretty much rivals in high school. And even when they had reconnected, they'd both kind of been in each other's friend zones. But hey, things can change.

.::.

That night after leaving Kurt's, Sebastian was invited to dinner with Jeff and Nick. Throughout their meal, he noticed how the two seemed to tease each other a lot, yet still had mutual respect. Sebastian decided that that was something he wanted. Maybe he'd have it with Kurt, maybe not. Only time would tell.


End file.
